I have one too!! but for tokyo, where no one ever considered a grid, they were just trying to create a labyrinth to confuse the ninja. I always know which way is north, but that doesn't actually mean I know where I am or where I am going.

Boston's street network was laid out logically to the original shorelines, hills, and direct paths to the water. As the hills were flattened and land made through filling the shoreline, what logic there was to the street layout became less and less perceptible. All the streets which once jogged the shoreline or hillside don't make much sense once that shoreline or hillside no longer exist!